Hydrochloric Acid → 3-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

HRID 870728노트

반응식

HRID 870728 반응식
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([Br:24])=[CH:22][N:23]=3)[N:20]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[ClH:1].[Br:24][C:21]1[N:19]2[N:20]=[C:15]([N:12]3[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)[CH:16]=[CH:17][C:18]2=[N:23][CH:22]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 686481214-(3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 866964333-Bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Concentrated hydrochloric acid (6.4 mL) was added to a solution of 4-(3-bromo-imidazo[1,2-b]pyridazin-6-yl)-piperazine-1-carboxylic acid tert-butyl ester 2.9 g, 7.6 mmol) in methanol (150 mL), allowed to stir at ambient temperature overnight, then evaporated to dryness. The resultant yellow solid was dissolved in methanol and the stirred solution diluted with diethyl ether to precipitate 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride as 2.6 g of white powder, mp. 275-276° C. (dec.). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.24 (br. s., 4H) 3.82-3.92 (m, 4H) 7.57 (d, J=10.11 Hz, 1H) 8.05 (s, 1H) 8.12 (d, J=10.10 Hz, 1H) 9.70 (br. s., 1H). 13C NMR (100 MHz, DMSO-d6) δ ppm 41.86, 42.37, 101.30, 114.15, 124.22, 127.20, 134.76, 155.43. LRMS (ESI) m/z 282.1/284.1 [(M+H)]+, calc'd for C10H12BrN5: 282.14.

후처리

  1. customevaporated to dryness
  2. dissolutionThe resultant yellow solid was dissolved in methanol
  3. additionthe stirred solution diluted with diethyl ether
  4. customto precipitate 3-bromo-6-piperazin-1-yl-imidazo[1,2-b]pyridazine dihydrochloride as 2.6 g of white powder, mp. 275-276° C. (dec.)

출처 및 근거

ORD 기록
ord-0892f9b3568a4f0599831a4389682aba
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969565B2

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